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$2,500,000
8 Beds ⋅ 4 Baths ⋅ 619978 MLS
Discover an exceptional investment opportunity in the heart of the Florida Keys! Situated on a spacious lot just 3 minutes from the beach and world-famous Duval Street, this unique multi-unit property offers versatility, comfort, and island-style living at its finest. The main residence features 5 bedrooms and 3 bathrooms across 2,432 total s/f, designed for both relaxation and entertaining. Enjoy a private pool with pool heater, along with the convenience of two elevated A/C units, both less than 4 years old. The second unit offers 3 bedrooms and 1 bathroom with 1,504 total s/f of living space, plus a 2-car garage and its own elevated A/C unit, also less than 4 years old. Built for peace of mind and modern living, the property includes a durable metal roof, impact windows throughout, camera security system, preparation for an electric vehicle charger, and separate electric and water meters for each unit. Whether you're seeking a primary residence, vacation retreat, or income-producing property, this rare Florida Keys gem combines location, flexibility, and outstanding features in one incredible package.

1409 Whalton St, Key West
$3,500,000
3 Beds ⋅ 3 Baths ⋅ 619959 MLS
Located within the quiet, gated security of Old Town Villas, this 3-bedroom, 3-bathroom townhome offers a sophisticated, low-maintenance island retreat just one block off of Duval St. Built in 2017, with solid concrete construction, this exceptional residence blends contemporary elegance with a thoughtfully designed layout that maximizes privacy, comfort, and functionality. Stepping inside, the interior is highlighted by beautiful tile flooring that runs seamlessly throughout. The main level features an open-concept layout with a spacious living room and chef's kitchen complete with stainless steel appliances and granite peninsula offering abundant prep space and casual seating. Just off the kitchen, a flexible-use room can serve as a dining area or private bedroom suite, complete with its own ensuite bathroom. A hallmark of this property is the extensive amount of premium, custom-built cabinetry and shelving installed throughout by the California Closets, offering unparalleled storage and organization. For effortless luxury, a private elevator services all four levels, transporting you from the two-car garage all the way to the rooftop terrace. The third floor hosts two spacious ensuite bedrooms, each featuring private balconies and large walk-in closets complete with custom organizational systems. The top floor is dedicated to an open living room and office area--a flexible bonus space filled with natural light. Step out from this upper lounge onto the spectacular rooftop terrace, equipped with custom awnings for comfortable shade, designed to capture both sunrise serenity and vibrant sunset views. For total peace of mind, the home features impact-rated windows and doors throughout. Beyond your front door, enjoy the exclusive community amenities, including a large pool and cabana. Conveniently situated near the very best dining and boutiques Key West has to offer, this home delivers the ultimate blend of privacy, location and the coveted Key West lifestyle.

141 Simonton St, Key West
$1,170,000
3 Beds ⋅ 3 Baths ⋅ 619952 MLS
Hidden away on one of Old Town's most storied streets, 1016 Varela St. Rear is the kind of Key West address that feels like a private discovery. Originally constructed in the 1920s, this piece of living Key West history has been thoughtfully renovated while honoring the character that only a century of island life can impart. Tucked discreetly behind the street, the fully restored 3-bedroom, 3-bathroom residence offers a rare sense of seclusion in the heart of historic Old Town -- without sacrificing a single step of the legendary walkability that defines this neighborhood. Duval Street, world-class dining, the harbor, and the full tapestry of Key West life are all moments away on foot. Arrive home to a covered front porch -- the quintessential Key West perch for morning coffee or evening cocktails. Inside, soaring cathedral ceilings flood the living spaces with light and volume, while refinished hardwood floors, an updated kitchen, and impact windows throughout speak to a renovation done with care and intention. The private rear yard offers room for a pool, a rare opportunity to create your own tropical retreat in the heart of Old Town. A separate upstairs apartment with its own private entrance offers exceptional flexibility: a sanctuary for a young adult, an elegant in-law suite, or an income-producing rental that helps carry the property. For the discerning buyer, two details stand above the rest: 1016 Varela Rear sits in an X flood zone -- the premier flood designation in the Keys, carrying no flood insurance requirement -- and the property carries an assumable VA loan, a remarkable financial advantage for qualified buyers in today's market. In Old Town Key West, a century-old home with this much flexibility and this little compromise is extraordinarily rare. Welcome to your hidden corner of paradise.

1016 Varela St Unit Rear, Key West
$1,675,000
5 Beds ⋅ 3 Baths ⋅ 619947 MLS
Welcome to 606 Grinnell Street located in the heart of Old Town Key West, this charming duplex offers the perfect blend of classic Key West character and flexible living opportunities. The first-floor unit features 2 nice sized bedrooms and 1.5 baths, while the spacious second-floor unit offers 3 bedrooms and 1 bath, complete with a private rear balcony overlooking the backyard oasis. Both units feature full sized kitchens with great dining spaces, as well as living rooms too. A welcoming front porch adds to the home's island charm, creating the perfect spot to relax and enjoy the neighborhood atmosphere. Step outside to your private backyard retreat featuring a sparkling pool for your relaxation, ideal for entertaining, time off, or enjoying the Key West lifestyle year-round. Whether you're looking for an investment property, multi-generational living, or the option to live in one unit while renting the other, this versatile Old Town property offers endless potential. There's a convenient side door entrance for the 2nd unit upstairs, while having a lockout door in the first unit if you wanted access to upstairs. Nice thought for Indoor or Outdoor Access to upstairs. Just moments from world-famous Duval Street with lots of dining options, historical seaport, shopping, and nightlife experiences.

606 Grinnell St, Key West
$2,345,000
5 Beds ⋅ 4 Baths ⋅ 619930 MLS
Prime Old Town Key West Location with 55 ft of Truman Avenue Frontage and Fantastic Off Street Parking. The property currently consists of four licensed rental apartments; one 2BR/1BA unit and three 1BR/1BA units. Flexible layout supports a variety of uses including long-term rentals, monthly vacation rentals, employee housing, or mixed-use potential with commercial use on the ground level and residential above. The property also offers the potential to be reimagined as a spacious single-family residence. (Buyer to verify) Property formerly configured for two business offices. Perfect for your business downstairs and reside upstairs. Generous off-street parking; a rare and valuable feature in Old Town, enhances desirability for business and/or residential occupants. Classic Conch-style construction with covered porches adds to the property's island appeal and long-term value. This is an extremely well-located property with multiple use possibilities. Buyer to verify any conversion from existing use.

1104 Truman Ave, Key West
$2,345,000
5 Beds ⋅ 4 Baths ⋅ 619927 MLS
FOUR UNIT Property in a Prime Old Town Key West Location with LOTS of OPTIONS! 1104 Truman Avenue is a legal four-unit property with multiple use possibilities. Generous off-street parking; a rare and valuable feature in Old Town, enhances desirability for business and/or residential occupants. Classic Conch-style construction with covered porches adds to the property's island appeal and long-term value. The property currently consists of one 2BR/1BA unit and three 1BR/1BA units, all licensed rentals.. Flexible layout supports a variety of uses including long-term rentals, monthly vacation rentals, employee housing, or mixed-use potential with possible commercial use on the ground level and residential above. The property also offers the potential to be reimagined as a spacious single-family residence. (Buyer to verify) This is an extremely well-located property with multiple use possibilities in a high-demand rental market.

1104 Truman Ave, Key West
$889,000
3 Beds ⋅ 2 Baths ⋅ 619926 MLS
Now offered at $889,000, this 2-bedroom, 2-bath Key West beachfront condo sits ground-floor at Key West by the Sea, directly across from Smathers Beach, a rare setup that lets you walk to the sand without stairs, elevators, or commuting. At 1,221 square feet, the 3BR deeded layout lives comfortably open, with room to actually use the space rather than just pass through it. Dual-zone split A/C allows personalized comfort. Hurricane-impact, soundproof windows and doors provide enhanced security, energy efficiency, and peace of mind all year long. Inside, luxurious porcelain flooring runs throughout, paired with detailed bathroom tile work chosen to match the quality of the rest of the home. The kitchen carries soft-touch cabinetry and granite countertops -- quiet, durable choices that hold up well in a beach environment, which matters more here than most out-of-state buyers realize until they've owned property in the Keys for a few years. Key West by the Sea is a managed beachfront community with resort-style amenities, meaning pool, grounds, and building upkeep are handled for you offering low-maintenance, turnkey ownership that buyers relocating from out of state especially value. The building has never flooded, a track record that matters as much as the view when you're evaluating waterfront property in the Florida Keys. This stretch of South Roosevelt Blvd sits between the Atlantic shoreline and the island's laid-back Old Town core, across the street from Smathers Beach, close to Key West International Airport, and minutes from Duval Street, the historic Bight, and Higgs Beach. It's the kind of setting where morning coffee happens on the terrace with saltwater air and pool views, evenings mean sunset over the water instead of a screen, and life moves at the pace islanders have always known: bike rides instead of traffic, conch culture instead of chain restaurants. That's the island lifestyle longtime locals like myself have watched hold its value for decades.

2601 S Roosevelt Blvd Unit APT 103C, Key West
$1,799,999
7 Beds ⋅ 5 Baths ⋅ 619911 MLS
Endless possiblities! Three units to rent for the investor or live in one and produce income from the other units. Downstairs you have a 3/1.5 with an open floor plan and covered porch with a patio. Upstairs you have two units with a 2/1 floor plan and a fire wall between units. All units have W/D hook ups and central air. Both units upstairs have balconies and seperate staircases for entry. Low maintence yardcare. Covered and dedicated parking with street parking as well. Great location close to downtown and the beaches. Owner is a general contractor and has lived in the home since 1972 and added the second story in 1994.

1504 Flagler Ave, Key West
$1,799,000
7 Beds ⋅ 5 Baths ⋅ 619904 MLS
Tucked into one of Old Town's most peaceful and charming pockets, this unique multi-unit property offers the perfect blend of classic Key West character and flexible living. At 800 Elizabeth Street, you'll find a quintessential two-story Conch home featuring 5 bedrooms and 3 bathrooms, soaring ceilings, and timeless architectural details. Start your mornings on the inviting front porch and wind down in the evenings on the upstairs balcony overlooking the quiet, tree lined street. Just steps away, 624 Petronia Street offers a well designed duplex with two separate 1-bedroom, 1-bath units: each complete with a full kitchen and private washer and dryer, making them ideal for guests, tenants, or extended family. Between the two homes, a welcoming shared patio creates the perfect setting for outdoor dining, grilling, and relaxed island living under the palms. Situated in a desirable X flood zone (one of the highest elevations in Key West) this property combines peace of mind with an unbeatable Old Town location close to everything, yet tucked away from the hustle. Whether you're seeking an income producing investment, a family compound, or a private island retreat with room for everyone, this rare offering captures the true spirit of Key West living.

800 Elizabeth St, Key West
$700
2 Baths ⋅ 619902 MLS
Hard to find small office space available in Old Town! Freshly updated professional offices 70 sf for $700+ per month. Join the friendly business environment at Key West Theater catering to local small business owners. Wifi, electric and water included.

524 Eaton St Unit 220, Key West
$7,500,000
5 Beds ⋅ 5 Baths ⋅ 619886 MLS
At the end of prestigious Sunrise Lane, where land meets open water on 3 sides, 3750 Sunrise Lane stands as one of the most extraordinary waterfront offerings in Key West. Properties of this scale and setting rarely exist, and almost never come to market. Originally built in the 1950s and extensively rebuilt in 1999, this legacy estate sits on a 28,500sf peninsula, offering a rare scale, privacy, and waterfront presence that is nearly impossible to replicate. The 5,378sf residence blends timeless architecture with expansive indoor and outdoor living. The main level features gracious living spaces with heart pine floors, French doors, and light-filled rooms opening to wide terraces and tranquil water views. The home offers 5 bedrooms and 4.5 baths, including 3 first-floor bedrooms and a spacious primary suite designed for comfort and privacy. Upstairs, 2 guest bedrooms open to a covered balcony and rare widow's walk with panoramic views of the Atlantic, Gulf, and surrounding protected lands. At the heart of the home is an expansive family-style kitchen with a large breakfast room, bar seating, desk area, and rich wood cabinetry. A handsome den with a built-in wet bar creates a warm gathering space, while a studio/flex room offers versatility as an office, art studio, fitness room, or guest overflow. The grounds are equally remarkable, featuring mature tropical landscaping, a large swimming pool, and over 3,200sf of brick patios. Nearly 500 linear feet of seawall provide exceptional dockage with a concrete dock and 2 boat lifts offering immediate deep-water access to both the Atlantic and Gulf. An oversized finished 828sf garage with 4 garage doors adds rare flexibility and functionality. This legacy estate awaits restoration and the vision of its next owner. Its setting, structure, and scale create a once-in-a-generation opportunity to reimagine one of Key West's most significant waterfront properties.

3750 Sunrise Ln, Key West
$1,350,000
1 Baths ⋅ 619883 MLS
Real estate only. No business included. By appointment only, do not disturb business. This commercial building sits on over 1 acre of land at the entrance to the Key West Golf Club community, just off College Road. Currently configured with large showroom, 7 offices, one ADA compliant full bath and reception area. Plenty of parking in adjoining parking lot, plus additional parking in rear. (Over 12 spaces) Close to Lower Keys Medical Center and quick access to US 1. The property will be delivered vacant at closing. Seller is a Florida real estate broker.

1 Golf Club Dr, Key West
$874,500
3 Beds ⋅ 3 Baths ⋅ 619867 MLS
A bougainvillea-covered trellis and cozy front gate welcome you! Charming, secluded island retreat overlooks the Key West Golf Course. Within the gated KW Golf Club community, this beautifully maintained home offers a rare combination of privacy, tropical ambiance, truly unique architectural features. One of the most exceptional attributes is its expansive wraparound verandas on both levels, a customized feature found in only 1 townhome building w/in the entire community. These divine outdoor living spaces create an extraordinary extension of the home w/seamless indoor-outdoor island living, panoramic tropical views, refreshing S.E./S.W. breezes flowing throughout. Spacious interior features: upgraded Italian ceramic tile on main level, luxury vinyl flooring on steps/upstairs, vaulted ceilings, creating an open atmosphere. Custom kitchen offers ceiling-height cabinetry, granite countertops, upgraded stainless appliances, generous prep space. French doors throughout the residence invite natural light into every room while enhancing the true ''island residence'' experience. Convenient powder rm. downstairs, separate washing machine/dryer closet. Spacious living/dining room areas, taller ceiling, 2 nautical fans, leading directly to an amazing, tranquil space. The lower-level tiled veranda, dual ceiling fans, functions beautifully as an additional entertaining area, more generous in size compared to most homes. Hidden behind layers of tropical foliage, the rear yard feels like a secret island garden. Expansive Boston brick patio, towering palms, soothing heated jacuzzi, reminiscent of a boutique resort tucked quietly along #2 tee box/fairway. Gentle tropical breezes, surrounding greenery provides privacy/serenity. The primary bdrm. is en-suite w/French doors opening onto expansive upper veranda. 2 guest bedrooms w/shared bath each w/French doors. Extraordinary opportunity to own a private tropical retreat, classic KW architecture charm, laid-back sophistication & more

56 Golf Club Dr, Key West
$515,000
3 Beds ⋅ 3 Baths ⋅ 619863 MLS
Five miles from Duval Street, priced below $425/sq ft, this is one of the best-value three-bedroom, three-bath homes available in the Key West area today. Tucked inside Harbor Shores on Stock Island, this home features 1,222 square feet of living space that works. Vaulted ceilings, granite countertops, central AC, and two rear bedrooms large enough for king beds. The stick-built Florida room addition gives you extra living space. Harbor Shores is a waterfront community with a private boat ramp and available dock rentals. For boaters, this is the kind of access that's getting harder to find at this price point. Stock Island offers marinas, restaurants, and the creative energy of a community that's authentically Keys without the Old Town price tag.

6800 Maloney Ave Unit 13, Key West
$849,900
3 Beds ⋅ 2 Baths ⋅ 619859 MLS
Welcome to island living in the highly sought-after Key West Golf Club community! This beautifully maintained home at 34 Golf Club Drive offers the perfect blend of comfort, upgrades, and convenience in a gated neighborhood just minutes from Old Town Key West. This light-filled home features an open-concept living area with soaring ceilings, luxury vinyl plank flooring, and sliding glass doors that bring the outdoors in. The updated kitchen offers quartz countertops, white cabinetry, stainless steel appliances, and a functional layout ideal for entertaining or everyday living. Thoughtful upgrades include impact windows on the front and back of the home, hurricane shutters for major entrances and side windows, spray foam insulation in the crawl space, and a newer air handler installed approximately five years ago. A new rear fence and gate provide direct access to the golf course, while peaceful views of the 5th and 6th holes and lagoon create a relaxing island atmosphere. The upstairs bedrooms feature beautiful vaulted ceilings, adding charm and an airy feel throughout the upper level. Outdoor spaces are surrounded by mature tropical landscaping, perfect for relaxing or entertaining. Additional highlights include a termite guarantee already in place for added peace of mind and an assumable VA loan with an exceptionally low 1.99% interest rate. Non-military buyers may also qualify to assume the loan if the property will be used as their primary residence, subject to lender approval and VA guidelines. Residents of the Key West Golf Club community enjoy access to resort-style amenities including two pools, a fitness center, gated security, and beautifully maintained grounds. Whether you're searching for a primary residence, second home, or investment opportunity, this property captures the essence of easy Key West living. Tenant until 5/31/26 24 hour notice needed

34 Golf Club Dr, Key West
$1,025,000
2 Beds ⋅ 2 Baths ⋅ 619778 MLS
This spacious two-bedroom, two-bath penthouse condo boasts a stunning balcony with ocean views, making it the perfect place to relax and enjoy the breathtaking scenery. The beautifully designed kitchen features a breakfast bar, granite countertops, and stainless steel appliances, making it a chef's dream come true. The stunning living room and dining room are flooded with natural light, creating a bright, inviting space perfect for entertaining guests. The floor-to-ceiling windows allow the natural light to pour in and are complemented by the soaring cathedral ceilings, which add an extra layer of grandeur and elegance to the space. Ample storage throughout ensures you'll have plenty of space to store all your belongings and keep your new home tidy and organized. The best feature of this penthouse is the breathtaking sunrises you'll enjoy over the Atlantic Ocean. Whether you're sipping your morning coffee or simply taking in the view, this condo will provide the perfect setting for relaxation and rejuvenation. The complex: One of the best parts of 1800 Atlantic is its private beach. You can soak up the sun, enjoy the stunning ocean views, or dip in the Olympic-sized heated pool while relaxing within this gated and secured oceanside community. For those who love staying active, three lighted tennis courts are perfect for a friendly game with friends or a competitive match, and the fitness center is fully equipped with everything you need to stay in shape and achieve your health goals. With storage and covered garage parking, you'll have plenty of space to keep all your belongings safe and secure. With its tropical resort-style setting and luxurious amenities, 1800 Atlantic is the perfect place to call home.

1800 Atlantic Blvd Unit 427C, Key West
$5,300
619760 MLS
326sf in Strip Center on Front Street across from Mallory Square, located on the busiest corner in Key West. Outstanding foot traffic from tourists, cruise ship passengers, sunset celebrations and locals. Join Haagen Dazs, Seabags & Green House. In addition to monthly base rent quoted are triple net charges and sales tax.

431 Front St Unit #5, Key West
$1,250,000
2 Beds ⋅ 2 Baths ⋅ 619758 MLS
With only two owners in its history, this well-maintained two-story property presents a rare investment opportunity in Key West. Configured as a legal duplex with two separately metered 1-bedroom, 1-bath units, it offers exceptional flexibility--ideal for investors seeking strong rental potential, business owners looking for employee housing, or owner-occupants wanting to offset costs by renting one unit while living in the other. Set on a 5,000 sq ft lot, the property is surrounded by lush, mature tropical landscaping with a wide variety of plants and palms, creating a private, shaded, treehouse-like setting filled with natural light. Two large screened porches and additional open-air spaces provide ideal indoor-outdoor living, while an outdoor shower enhances the island lifestyle. The home has been thoughtfully updated and well cared for, featuring Mitsubishi mini-split A/C systems in both units, a new hot water heater, new ceiling fans, impact windows upstairs, new gutters, updated appliances, and soft-close cabinetry. Interior finishes include a mix of pine, vinyl, and concrete flooring, along with stainless, Formica, and butcher block countertops. Both units offer full bathrooms with tubs. Additional highlights include two off-street parking spaces, low-maintenance grounds, and multiple windows throughout for abundant natural light and airflow. Located in desirable Midtown East, just minutes from everything Key West has to offer, this is a versatile, income-producing property with strong upside potential.

1911 Seidenberg Ave, Key West
$1,995,000
619755 MLS
1202 Simonton Street sits in the heart of Old Town, South of Truman, four blocks from the Southernmost Point. This corner has been home to some of Key West's most recognized restaurants & the bones know what this building is capable of. If you're looking for a commercial building in Old Town Key West that offers: a 4,366-square-foot CBS building on a 4,700-square-foot corner lot, zoned Historic Neighborhood Commercial, on one of the island's most walkable and high-traffic corridors, delivered in shell condition and ready for a buyer who knows exactly what they want to build. Look no further.

1202 Simonton St, Key West
$575,000
3 Beds ⋅ 2 Baths ⋅ 619747 MLS
Experience the relaxed charm of island living in this nicely updated third-floor 3-bedroom, 2-bath condo located in the highly desirable Las Salinas community. Filled with natural light, the open-concept layout creates a bright and welcoming atmosphere that feels comfortable from the moment you walk in. The thoughtfully designed kitchen features quartz countertops, stainless steel appliances, and a convenient washer/dryer combo, all opening to a spacious living and dining area perfect for entertaining or simply unwinding after a day on the water. Step outside to your private balcony overlooking the community pool -- an ideal spot for morning coffee, peaceful evenings, and enjoying the island breeze. The primary suite includes a private en-suite bath, while the additional bedrooms offer generous closet space for comfortable everyday living. An exterior storage locker provides extra room for bikes, beach gear, and all your island essentials, adding even more practicality and value. Residents of Las Salinas enjoy resort-style amenities including a large sun-drenched swimming pool, newly updated fitness center, bike storage, and lush tropical landscaping -- all with one of the lowest HOA fees in Key West, including insurance. Ideally located on the east side of the island, you're just moments from Smathers Beach, restaurants, shopping, and Key West International Airport. The nearby scenic promenade along the Atlantic Ocean is perfect for biking, jogging, or taking peaceful morning walks while enjoying breathtaking Keys sunrises. Whether you're searching for a full-time residence, vacation getaway, or smart investment property, this condo offers the easygoing lifestyle people dream about when they think of Key West.

3930 S Roosevelt Blvd Unit N304, Key West
$549,000
2 Beds ⋅ 2 Baths ⋅ 619744 MLS
Located in a family-friendly neighborhood with no HOA or dues, this well-maintained townhome offers both comfort and convenience. Centrally situated within walking distance to schools, grocery stores, and local baseball and football fields, it's an ideal setting for everyday living. The main level features a functional layout with a bright living area, kitchen, and a half bathroom with laundry hookups. The living room offers flexibility and can be easily converted into a third bedroom if desired. Upstairs, you'll find two spacious, light-filled bedrooms with ample closet space, along with a full bathroom. The home also includes off-street parking and a fully fenced yard, providing added privacy. Move-in ready, this property is a great opportunity for homeowners or investors alike.

3204 Harriet Ave, Key West
$2,445,000
2 Beds ⋅ 3 Baths ⋅ 619742 MLS
Discover a rare blend of history, artistry, and luxury in this extraordinary residence at the celebrated William Fleming House--one of Old Town Key West's most iconic and meticulously restored historic buildings. Originally constructed in the 1890s as Peacon's General Store, this architectural treasure has been transformed into an exclusive boutique condominium, exquisitely and entirely renovated. Inside, the first level condo rises to an unforgettable 16 feet, creating a sense of openness and serenity that feels both dramatic and inviting. Sunlight pours through impact-rated windows and doors, illuminating the vintage wood flooring and expansive walls that are ideal for showcasing meaningful art and personal collections. The thoughtfully designed layout includes two bedrooms, two full bathrooms, a half bath and a versatile loft space- accessed by a traditional staircase--offering remarkable flexibility for work, guests, creative pursuits, or quiet retreat. A private outdoor deck extends your living space and provides a peaceful spot for morning coffee or evening unwinding. The William Fleming House elevates daily living with its heated outdoor pool, lush tropical landscaping, and assigned off-street parking. Located in the desirable X-flood zone and directly across from Williams Hall, this residence places you in the heart of Old Town's cultural and architectural richness. With its unmatched scale, history, and character, this home invites you to bring your vision and transform it into a truly exceptional Key West sanctuary--one that reflects your style, your story, and your sense of place.

800 Fleming St Unit Unit C1, Key West
$1,299,000
4 Beds ⋅ 2 Baths ⋅ 619738 MLS
FLIP FLOPS INLCUDED! Some homes are just addresses. This one is a lifestyle. Tucked into the heart of Old Town Key West, this beautiful historic Conch home is wrapped in the warmth of original Dade County pine and rich hardwood floors -- the kind of craftsmanship that simply isn't built anymore. The main house offers three bedrooms and a fully renovated bath, anchored by a large kitchen with generous cabinet space.. A fully enclosed porch is your place for morning coffee, chatting around the table or dining while overlooking the pool. Central air conditioning keeps things cool. Every window and door has been upgraded to impact, giving you peace of mind alongside the charm. Step outside and the magic continues. A sparkling pool with a waterfall feature and Trex decking invites you to linger. An outdoor shower makes coming in from the water effortless. The fully fenced front and back yards create a private tropical sanctuary, and off-street parking -- a true luxury in Old Town -- takes the stress out of coming home. The guest cottage is its own retreat, offering one bedroom, one bath, and a Murphy bed that makes the space as flexible as your plans. Whether it becomes a private getaway for family and friends, a creative studio or a detached office, it gives this property a versatility that is genuinely rare. The location is the final piece that makes everything click. A ten-minute walk from Duval Street -live music, art galleries, open-air restaurants, theaters and the electric pulse that makes Key West unlike anywhere else on earth. 7 minutes the other way brings you to the White Street District know for Fausto's Food Palace, where locals have shopped for generations, and the legendary Sandy's Café. This property comes fully turn-key, bedding, housewares, pool toys, bicycles, and yes, flip flops are included. Whether you wanting a second home, a monthly vacation rental or simply ready to walk through the door and start living living in paradise.

928 United St, Key West
$9,888,000
3 Beds ⋅ 2 Baths ⋅ 619724 MLS
Fabulous Find on the Atlantic Side of Key West! Welcome to a truly unique opportunity in the heart of Key West. As the last and only remaining undeveloped property in the Historic Commercial Tourist District (HCT zone), this listing presents a rare and final chance to create something extraordinary. Imagine waking up to breathtaking, unobstructed ocean and beach views every day. Seabirds passing overhead, gentle breezes arriving at your lanai--it's an experience like nowhere else. This is island living at its finest! Permitted HCT uses include: Single-family and two-family residential dwellings, Multiple-family residential dwellings, Restaurant, Business and professional offices, Hotels, Motels, transient lodging, and more. This two-story home comes equipped with two separate electric meters. This exceptional property is truly one of a kind, with no identical or closely similar listings anywhere in Key West. The ideal circumstances are here and now-- an unparalleled combination of an oversized ocean-view lot, located just three blocks from Duval Street, the gateway to downtown. Spanning 8,700 square feet, this property offers ample space for your creative vision, whether you dream of building a luxurious residence, alongside a commercial venture boutique hotel, or restaurant, -- this and more are supported by HCT zoning. This property is all about the excitement of shaping a new vision for a future in paradise. Let your imagination run wild and transform this blank canvas into something extraordinary. Don't miss out on this once-in-lifetime opportunity--call today for your private tour and start envisioning your future in Key West!

1430 Vernon Ave, Key West
$1,875,000
4 Beds ⋅ 3 Baths ⋅ 619723 MLS
DUPLEX! Discover the breathtaking corner property at Sunrise Shores, set on an expansive lot exceeding 13,000 square feet. POOL! The main residence offers over 1,750 square feet of living space, complemented by a detached guest cottage of 640 square feet. This meticulously maintained property has been cherished by its owners. The main home features three bedrooms and two bathrooms. It boasts a thoughtfully designed layout that includes a spacious family room and a large living room with a fireplace that opens up to the lanai. The primary bedroom provides direct access to the pool area and features an updated bathroom and a generous walk-in closet. The second bedroom also opens to the pool area, while the third bedroom is conveniently located next to the updated hall bath. There is also a laundry room with additional storage space. The detached guest cottage includes one bedroom and one bathroom. This property is perfect for owner-occupiers, investors, multi-generational living, and more.

1516 17th Ter, Key West
$2,900,000
2 Beds ⋅ 2 Baths ⋅ 619715 MLS
Seclusion meets striking contemporary design in this elevated sanctuary, positioned just moments from Higgs Beach and White Street Pier. Behind a signature pivoting red gate and architectural peekaboo wall, the residence unfolds as a curated experience of light and geometry. The entry foyer--anchored by a sun-drenched desk nook and an open-tread staircase--leads to a living space defined by floor-to-ceiling glass and transom detailing that frames the outdoor oasis like a living gallery. The culinary space is anchored by a sleek, minimalist aesthetic, featuring custom cabinetry, crisp white surfaces, and Bosch appliances. A glass-door pantry provides a sophisticated home for provisions, blending functional utility with the kitchen's clean geometry For guests, a private main-level suite is tucked away behind a discreet pocket door, offering an ensuite bathroom and ample closet space for a completely independent wing. The second floor is dedicated entirely to the primary retreat. This suite features a large walk-in closet and a refined ensuite bathroom. Just beyond the sleeping quarters is a private balcony where an open-air soaking tub offers a quiet moment of luxury under the stars. The exterior of the home is a masterwork of tropical landscaping, where beautifully mature and lush greenery wraps the property in total privacy. At the heart of the grounds is an expansive heated pool bordered by a large deck, perfect for sun-drenched afternoons. For the host, the covered outdoor dining pavilion is fully equipped with an integrated grill and ample countertop space for seamless entertaining. Nearby, a serene Zen garden with a tranquil fountain feature provides a quiet corner for meditation and reflection. This is more than a home; it is a sophisticated, high-design haven just steps from the ocean.

1701 Laird St, Key West
$1,700,000
4 Beds ⋅ 4 Baths ⋅ 619703 MLS
Strong value-add multifamily fourplex investment opportunity with major capital improvements already completed. The property offers four two-bedroom residences totaling approximately 3,000 square feet, with each unit comprising approximately 750 square feet. The lower level includes two residences, while the upper level features two additional residences with approximately 960 square feet of combined balcony space. Major improvements include a new standing-seam metal roof, new impact-resistant windows and doors throughout, and completed concrete, stucco, and exterior work. The property is ready for the next owner to complete the remaining work and execute their preferred investment strategy. Once completed and delivered furnished, the property is projected to have the potential to generate more than $200,000 in annual gross rental income across all four units. Additional potential may include condominium conversion, subject to all applicable approvals and requirements. A compelling opportunity to complete, stabilize, and maximize a well-positioned Key West income-producing asset.

1224 2nd St, Key West
$1,799,000
7 Beds ⋅ 5 Baths ⋅ 619700 MLS
Tucked into one of Old Town's most peaceful and charming pockets, this unique multi-unit property offers the perfect blend of classic Key West character and flexible living. At 800 Elizabeth Street, you'll find a quintessential two-story Conch home featuring 5 bedrooms and 3 bathrooms, soaring ceilings, and timeless architectural details. Start your mornings on the inviting front porch and wind down in the evenings on the upstairs balcony overlooking the quiet, tree lined street. Just steps away, 624 Petronia Street offers a well designed duplex with two separate 1-bedroom, 1-bath units: each complete with a full kitchen and private washer and dryer, making them ideal for guests, tenants, or extended family. Between the two homes, a welcoming shared patio creates the perfect setting for outdoor dining, grilling, and relaxed island living under the palms. Situated in a desirable X flood zone (one of the highest elevations in Key West) this property combines peace of mind with an unbeatable Old Town location close to everything, yet tucked away from the hustle. Whether you're seeking an income producing investment, a family compound, or a private island retreat with room for everyone, this rare offering captures the true spirit of Key West living.

800 Elizabeth St, Key West
$1,875,000
4 Beds ⋅ 3 Baths ⋅ 619698 MLS
Discover the breathtaking corner property at Sunrise Shores, set on an expansive lot exceeding 13,000 square feet. POOL! The main residence offers over 1,750 square feet of living space, complemented by a detached guest cottage of 640 square feet. This meticulously maintained property has been cherished by its owners. The main home features three bedrooms and two bathrooms. It boasts a thoughtfully designed layout that includes a spacious family room and a large living room with a fireplace that opens up to the lanai. The primary bedroom provides direct access to the pool area and features an updated bathroom and a generous walk-in closet. The second bedroom also opens to the pool area, while the third bedroom is conveniently located next to the updated hall bath. There is also a laundry room with additional storage space. The detached guest cottage includes one bedroom and one bathroom. This property is perfect for owner-occupiers, investors, multi-generational living, and more.

1516 17th Ter, Key West
$2,590,000
3 Beds ⋅ 2 Baths ⋅ 619667 MLS
Welcome to your Key West waterfront retreat. This 3bedroom 2bath home is featuring key upgrades already in place with a new roof, all new windows, updated electrical, fresh paint, and a beautiful brand new pool. Situated on an oversized 9,794 sq ft lot with room for your boat this home offers the ideal blend of comfort, outdoor living, and the flexibility to personalize over time. A rare opportunity to step into waterfront living in one of Key West's most desirable locations.

3612 Sunrise Dr, Key West